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GB1043141A - Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes and their therapeutically active non-toxic acid addition salts and the preparation thereof - Google Patents

Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes and their therapeutically active non-toxic acid addition salts and the preparation thereof

Info

Publication number
GB1043141A
GB1043141A GB24824/63A GB2482463A GB1043141A GB 1043141 A GB1043141 A GB 1043141A GB 24824/63 A GB24824/63 A GB 24824/63A GB 2482463 A GB2482463 A GB 2482463A GB 1043141 A GB1043141 A GB 1043141A
Authority
GB
United Kingdom
Prior art keywords
chloro
fluorophenyl
phenyl
cyclopropyl
prepared
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB24824/63A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Research Laboratorium C Janssen NV
Original Assignee
Research Laboratorium C Janssen NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Research Laboratorium C Janssen NV filed Critical Research Laboratorium C Janssen NV
Publication of GB1043141A publication Critical patent/GB1043141A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Wire Processing (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises 1-R1-2-R2-3-R3-4-oxo - 8 - R4 - 1,3,8 - triaza - spiro(4,5)decanes and the therapeutically active non-toxic acid-addition salts thereof, wherein R1 is a phenyl, lower alkaryl, lower alkyl, lower alkoxyphenyl, cycloalkyl or halophenyl radical; R2 is a hydrogen atom or a lower alkyl radical; R3 is a hydrogen atom or a hydroxymethyl, lower alkyl, lower alkoxycarbonylalkyl, cyanoalkyl, lower alkoxymethyl, lower alkylcarbonyl, carbamoylalkyl, cyclopropylcarbonyl, benzyl or benzoyl radical; R4 is an (R111)(R1111)CH- or Z(CH2)nradical, wherein R111 is a methyl or ethyl radical, R1111 is an aryl or arylethyl radical, n is a positive integer from 1 to 5 and Z is a lower alkyl, hydroxy, hydroxy-lower alkoxy, phenyl, diphenyl-cyanomethyl, diaryl-hydroxymethyl, diphenyl - propionylmethyl, fluorophenyl - hydroxymethyl, aryloxy, 1,4-benzodioxanyl, halo - 1,4 - benzodioxanyl, thienyl, halophenyl, lower alkylphenyl, tri-fluoromethylphenyl, pyridyl, di-lower alkyl-phenyl, lower alkoxyphenyl, cyclopropyl-ethenyl, benzoyl, halobenzoyl, thienoyl, lower alkoxybenzoyl, lower alkylbenzoyl, benzoyloxy, benzyloxy, phenylmethoxymethyl, phenyl-hydroxymethyl, fluorophenyl-lower alkyl-carb-onyloxy -methyl, aryl - cyclopropyl, arylthio, (aryl)(R1)CH-, wherein R1 is a lower alkyl, aryl or aralkyl radical, (aryl)2CH-O-, (lower alkyl)2C=CH-, or (aryl)(R11)C=CH-, where-in R11 is a hydrogen atom or a lower alkyl, aryl or aralkyl radical; said lower alkyl and lower alkoxy groups containing from 1 to 6 carbon atoms and said aryl radical being a phenyl, halophenyl, lower alkylphenyl, lower alkoxy phenyl, trifluoromethylphenyl or 2-thienyl radical. These compounds may be prepared by condensation of a piperidone-4 or 4-hydroxy piperidine alkali metal sulphite appropriately protected at the nitrogen atom by, for example, a benzyl group, with a primary amine and an alkali metal cyanide, conversion of the resulting 1 - substituted - 4 - cyano - 4 - secondary - amino piperidine to the corresponding carboxamide by acid hydrolysis of the nitrile function, cyclization of the carboxamide and, where necessary, saturation of the cyclic double bond at the 2,3-position. Cyclization may be effected by treatment with formamide, in the absence or presence of an inorganic acid, to yield the 1,3,8 - triazo - spiro(4,5)dec - 2 - ene in cases where the secondary amino group attached to the piperidine ring is alkyl-substituted, and the 1,3,8-triazo-spiro(4,5)decane where the secondary amino group is aryl-substituted. An exception occurs when the alkyl group is ethyl, in which case the saturated spiro compound is obtained. Alternatively cyclization may be effected by treatment of the carboxamide with triethoxymethane, in which case a 1,3,8-triazospiro(4,5)dec-2-ene is invariably obtained, or by treatment with an acylating agent, in which case the unsaturated 1,3,8-triazo-spiro(4,5)dec-2-ene bearing a substituent at the 2-position identical to the aliphatic carboxylic acid residue of the anhydride employed is obtained. Saturation of the cyclic double bond may be achieved by hydrogen activated by a catalyst, e.g. a platinum or nickel catalyst. The 1,2-disubstituted 1,3,8 - triaza - spiro(4,5)dec - 2 - enes bearing a methyl substituent at the 2-position or the corresponding compound unsubstituted at the 2-position may be advantageously reduced to the spiro(4,5)decane by treatment with a di-light metal hydride, e.g. LiAlH4 or NaAlH4. The benzyl group on the piperidine nitrogen atom may be removed by hydrogenolysis and then replaced by a variety of substituents by reaction of the appropriate halogenated reactant in the presence of a halogen acid acceptor. The debenzylation procedure is applicable to the 2,3-substituted, unsubstituted and 1-substituted compounds except for side reactions such as simultaneous dehalogenation if, for example, the 1-position is occupied by a haloaryl group. In the case of 2-methyl-substituted dec-2-enes debenzylation may be carried out before or after saturation of the cyclic double bond. Substituents may be introduced into the nitrogen group at the 3-position before or after debenzylation. For example, reaction with an anhydride introduces an acyl group, reaction with alkyl halide or quaternary ammonium alkylaryl halide introduces an alkyl group, reaction with an aqueous aldehyde introduces hydroxyalkyl group and reaction with an unsaturated nitrile introduces a cyanoalkyl group. 1 - Bromo - 1 - (4 - fluorophenyl) ethane is prepared by reacting 1-(4-fluorophenyl) ethanol with hydrogen bromide. 1-Bromo-1-(4-fluorophenyl) propane is similarly prepared. 1 - Chloro - 4 - (4 - methylphenyl) pentane is prepared by hydrogenating 5 - chloro - 2 - (4-methylphenyl) -2 - pentene. 1 - Bromo - 4 - (4-fluorophenyl) pentane, 1 - chloro - 4 - (4 - methoxyphenyl) pentane, 1 - chloro - 4 - (4 - chlorophenyl) pentane, 1 - chloro - 4,4 - diphenylbutane, 1 - chloro - 5,5 - diphenyl pentane, 1-chloro -4 - (4 - methylphenyl) - 4 - phenyl - butane, 1 - chloro - 4 - (4 - methoxyphenyl) - 4 - phenylbutane, 1 - chloro - 4 - (4 - fluorophenyl) - 4 - phenyl - butane, 1 - chloro - 5 - (4 - fluorophenyl) - 5 - phenyl - pentane, 1 - chloro - 4 - (4 - fluorophenyl) - 4 - (4 - methylphenyl) - butane, 1 - chloro - 4,4 - di -(4 - fluorophenyl) - butane, 1 - chloro - 5,5 - di -(4 - fluorophenyl) - pentane, 1 - chloro - 4 - (4 - fluorophenyl) - 4 - (3 - trifluoromethylphenyl) - butane, 1 - bromo - 4,4 - di - (3 - trifluoromethylphenyl) - butane, 1 - butane, 1 - chloro - 5 - (4 - fluorophenyl) - 4 - phenyl - pentane and 1 - chloro - 4,5 - di - (4 - fluorophenyl) - pentane are similarly prepared. 1 - Bromo - 2 - (4 - fluorophenyl) propane is prepared by reacting fluorobenzene with allyl bromide. 4 - Chlorophenyl - cyclopropyl - methyl - carbinol is prepared by reacting 4-chlorophenyl-cyclopropyl ketone with methylmagnesiumiodide and decomposing the product with an ammonium chloride solution. Cyclopropylmethyl - 4 - methylphenyl - carbinol, cyclopropyl-4 - methoxyphenyl - methyl - carbinol, cyclopropyl - 4 - methylphenyl - phenyl - carbinol, cyclopropyl - 4 - methoxyphenyl - phenyl - carbinol, cyclopropyl - 4 - fluorophenyl - phenylcarbinol, cyclopropyl - 4 - fluorophenyl - 4 - methylphenyl - carbinol, cyclopropyl - 4 - fluorophenyl-3 - trifluoromethylphenyl - carbinol, cyclopropyl-4 fluorophenyl - 2 - thienyl - carbinol, cyclopropyl - 2 - (4 - fluorophenyl) - 1 - phenyl - ethanol, 1 - cyclopropyl - 1,2 - di - (4 - fluorophenyl)-ethanol, cyclopropyl - phenyl - 3 - trifluoromethylphenyl - carbinol, cyclopropyl - 4 - fluorophenyl-4 - methoxyphenyl - carbinol, 4 - chlorophenyl-cyclopropyl - 4 - fluorophenyl - carbinol, cyclopropyl - 4 - fluorophenyl - 2 - thienyl - carbinol and 5 - chloro - 1 - (4 - fluorophenyl) - 1 - phenyl-pentanol are similarly prepared. 1 - Bromo - 1 - (4 - chlorophenyl) propane is prepared by reacting 1-(4-chlorophenyl) propanol with phosphorus tribromide. 1-Bromomethyl - 2 - phenyl - cyclopropane and 1 - bromo-2 - (4 - fluorophenyl) butane are similarly prepared. 5 - Chloro - 2 - (4 - chlorophenyl) - 2 - pentene is prepared by the action of thionyl chloride on cyclopropyl - 4 - chlorophenyl - methyl - carbinol. 4 - Chloro - 1 - (4 - fluorophenyl) - 1 - butene, 5 - chloro - 2 - (4 - methylphenyl) - 2 - pentene, 5 - chloro - 2 - (4 - methoxyphenyl) - 2 - pentene, 4 - chloro - 1 - (4 - fluorophenyl) - 1 - (4 - methylphenyl) - 1 - butene, 4 - chloro - 1,1 - di - (4-fluorophenyl) - 1 - butene, 4 - chloro - 1 - (4-fluorophenyl) - 1 - (3 - trifluoromethylphenyl) - 1 - butene, fluorophenyl) - 2-phenyl - 2 - pentene, 5 - chloro - 1,2 - di -(4-fluorophenyl) - 2 - pentene, 4 - chloro - 1 - phenyl - 1 -(3 - trifluoromethylphenyl) - 1 - butene, 4 - chloro-1,1 - di -(4 - methylphenyl) - 1 - butene, 4 - chloro-1 1 - (4 - fluoropheny - 1 - (4 - methoxyphenyl) - 1 -butene, 4 - chloro - 1 - (4 - chlorophenyl) - 1 - (4-fluorophenyl) - 1 - butene, 4 - chloro - 1 - (4-fluorophenyl) - 1 - (2 - thienyl) - 1 - butene, 4-chloro - 1 - (4 -methylphenyl) - 1 - phenyl - 1-butene, 4 - chloro - 1 - (4 - methoxyphenyl) - 1-phenyl - 1 - butene and 4 - chloro - 1 - (4 - fluorophenyl) - 1 - phenyl - 1 - butene are prepared similarly. 5 - Bromo - 2 - phenyl - 2 - pentene is prepared by the action of hydrogen bromide on 1-cyclopropyl-1-phenyl ethanol. 5-Bromo-2-(4-fluorophenyl) - 2 - pentene and 4 - bromo 1,1 - di - (3-trifluoromethylphenyl) - 1 - butene are prepared similarly. 5 - Chloro - 1,1 - diphenyl pentanol is prepared by reacting 5-chloro valerate with phenyl-magnesium bromide and decomposing the product with an ammonium chloride solution. 5 - Chloro - 1,1 - di - (4 - fluorophenyl) - pentanol, cyclopropyl - di - (3 - trifluoro - methylphenyl)-carbinol and cyclopropyl - di - (4 - methylphenyl)-carbinol are prepared similarly. 5 - Chloro - 1,1 - diphenyl - 1 - pentene is prepared by the action of concentrated hydro-chloric acid on 5-chloro-1,1-diphenyl pentanol. 5 - Chloro - 1 - (4 - fluorophenyl) - 1 - phenyl - 1-pentene and 5 - chloro - 1,1 - di - (4 - fluorophenyl)-1-pentene are prepared similarly. 1 - Chloro - 4 - (4 - fluorophenyl) - 4 - (2 - thienyl) butane is prepared by reacting cyclopropyl-4 - fluorophenyl -2 - thienyl - carbinol with perchloric acid to form 4 - (4 - fluorophenyl) - 4 -(2 - thienyl) - but - 3 - en - 1 - ol, reducing this compound with lithium tetra-hydroaluminate and treating the resulting 4-(4 - fluorophenyl) - 4 -(2 - thienyl) butanol with thionyl chloride. 1 - Chloro - 3 - (4 - methyl - thio - phenoxy)-propane is prepared by reacting 1-bromo-3-chloro-propane with 4-methyl thiophenol. 2-(4 - Fluoro - thio - phenoxy) -ethanol is similarly prepared. 1 - Chloro - 2 - (4 - fluoro - thio - phenoxy)-ethane is prepared by reacting 2-(4-fluoro-thio-phenoxy)-ethanol with thionyl chloride. 4 - Chloro - 1,1 - di - (4 - methoxyphenyl) - 1-butene is prepared by reacting
GB24824/63A 1962-06-22 1963-06-21 Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes and their therapeutically active non-toxic acid addition salts and the preparation thereof Expired GB1043141A (en)

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US20462362A 1962-06-22 1962-06-22

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Country Status (9)

Country Link
BE (1) BE633914A (en)
CH (1) CH462835A (en)
DE (1) DE1470125C3 (en)
DK (1) DK119880B (en)
FI (1) FI46967C (en)
FR (6) FR1573808A (en)
GB (1) GB1043141A (en)
NO (1) NO117368B (en)
SE (1) SE311019B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361889A1 (en) * 1975-07-21 1978-03-17 Janssen Pharmaceutica Nv NEW DERIVATIVES OF 1- (BENZAZOLYALCOYL) PIPERIDINE
US4080328A (en) * 1971-07-13 1978-03-21 Sumitomo Chemical Company, Limited N-substituted heterocyclic derivatives and preparation thereof
WO1999059997A1 (en) * 1998-05-18 1999-11-25 Novo Nordisk A/S Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes
EP0997464A1 (en) * 1998-10-23 2000-05-03 Pfizer Inc. 1,3,8-Triazaspiro[4,5] decanone compounds as orl1-receptor agonists
US6277991B1 (en) 1998-05-18 2001-08-21 Novo Nordisk A/S 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes
US6716846B2 (en) * 1998-07-27 2004-04-06 Schering Corporation High affinity ligands for nociceptin receptor ORL-1
US8394804B2 (en) 2001-10-19 2013-03-12 Janssen Pharmaceutica N.V. Phosphonic acid compounds as inhibitors of serine proteases
EP3138841A1 (en) * 2010-06-18 2017-03-08 Altos Therapeutics, LLC D2 antagonists, methods of synthesis and methods of use
IT201800007580A1 (en) * 2018-07-27 2020-01-27 Maria Cecilia Hospital Spa 1,3,8-triazaspiro compounds and their use as medicaments

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE792187A (en) * 1971-12-03 1973-03-30 Sumitomo Chemical Co NEW ALKYLAMINE DERIVATIVES
NZ181256A (en) * 1975-07-21 1978-04-28 Janssen Pharmaceutica Nv 1-(w-benzazol-11-ylalkyl)-piperidine derivatives and pharmaceutical compositions containing certain of these derivatives
DK139684A (en) * 1983-04-11 1984-10-12 Janssen Pharmaceutica Nv N-aryl-alpha-amino carboxamides
US5703088A (en) * 1989-08-21 1997-12-30 Beth Israel Deaconess Medical Center, Inc. Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses
US5244902A (en) * 1989-08-21 1993-09-14 Beth Israel Hospital Association Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses
US5574041A (en) * 1990-03-16 1996-11-12 Beth Israel Hospital Association Use of spiperone derivatives as immunosuppressant agents
US5693645A (en) * 1992-12-23 1997-12-02 Beth Israel Deaconess Medical Center, Inc. Use of spiperone or spiperone derivatives as immunosuppressant agents
DE19610397A1 (en) * 1996-03-16 1997-09-18 Krewel Meuselbach Gmbh Production of fluspirilene suspensions
DE102005038141A1 (en) * 2005-08-12 2007-02-15 Grünenthal GmbH Substituted 8- (3-aminopropyl) -1-phenyl-1,3,8-triaza-spiro [4.5] decan-4-one derivatives

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080328A (en) * 1971-07-13 1978-03-21 Sumitomo Chemical Company, Limited N-substituted heterocyclic derivatives and preparation thereof
FR2361889A1 (en) * 1975-07-21 1978-03-17 Janssen Pharmaceutica Nv NEW DERIVATIVES OF 1- (BENZAZOLYALCOYL) PIPERIDINE
WO1999059997A1 (en) * 1998-05-18 1999-11-25 Novo Nordisk A/S Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes
US6277991B1 (en) 1998-05-18 2001-08-21 Novo Nordisk A/S 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes
US6716846B2 (en) * 1998-07-27 2004-04-06 Schering Corporation High affinity ligands for nociceptin receptor ORL-1
US7094784B2 (en) 1998-07-27 2006-08-22 Schering Corporation High affinity ligands for nociceptin receptor ORL-1
EP0997464A1 (en) * 1998-10-23 2000-05-03 Pfizer Inc. 1,3,8-Triazaspiro[4,5] decanone compounds as orl1-receptor agonists
US8394804B2 (en) 2001-10-19 2013-03-12 Janssen Pharmaceutica N.V. Phosphonic acid compounds as inhibitors of serine proteases
EP3138841A1 (en) * 2010-06-18 2017-03-08 Altos Therapeutics, LLC D2 antagonists, methods of synthesis and methods of use
IT201800007580A1 (en) * 2018-07-27 2020-01-27 Maria Cecilia Hospital Spa 1,3,8-triazaspiro compounds and their use as medicaments
WO2020021378A1 (en) * 2018-07-27 2020-01-30 Maria Cecilia Hospital S.P.A. 1,3,8-triazaspiro compounds and their use as medicaments for the treatment of reperfusion injury

Also Published As

Publication number Publication date
FR2988M (en) 1964-12-07
SE311019B (en) 1969-05-27
DE1470125C3 (en) 1980-07-10
FR3059M (en) 1965-01-11
FR3043M (en) 1965-01-04
DK119880B (en) 1971-03-08
FR2986M (en) 1964-12-07
CH462835A (en) 1968-09-30
NO117368B (en) 1969-08-04
FR2987M (en) 1964-12-07
BE633914A (en)
FI46967C (en) 1973-08-10
DE1470125A1 (en) 1969-05-08
DE1470125B2 (en) 1979-10-31
FI46967B (en) 1973-05-02
FR1573808A (en) 1969-07-11

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